Method for preparing halogenated imidazopyridine derivatives

ABSTRACT

in which the specified structural elements have the definitions stated.

The present invention relates to a method for preparing halogenatedimidazopyridine derivatives of the formula (II)

proceeding from compounds of the formula (I)

via intermediates of the formula (IVa) or (IVb)

in which the structural elements shown in the formulae (I), (II), (IVa)and (IVb) have the definitions stated below.

The invention further relates to such halogenated imidazopyridinederivatives, and also intermediates and the reaction products ofcompounds of the formula (II) to give compounds of the formula (III)

in which the specified structural elements have the definitions statedbelow.

Halogenated imidazopyridine derivatives of the formula (II) are of greatindustrial significance for the pharmaceutical and agrochemical industryand are, for example, important intermediates, inter alia, in thepreparation of compounds that are effective as pesticides for example.

Imidazopyridines for use as pesticides and methods for the preparationthereof are described, for example, in WO 2010/125985, WO 2012/074135,WO 2012/086848, WO 2013/018928, WO 2013/191113, WO 2015/000715, WO2016/124563, WO 2016/124557, WO 2015/121136, WO 2015/133603, WO2015/198859, WO 2015/002211, WO 2015/071180, WO 2016/023954, WO2016/020286, WO 2016/046071, WO 2016/058928; WO 2016/116338, WO2016/107831, WO 2016/129684, WO 2017/055185, WO 2017/068599 and WO2016/125621. However, the prior art does not disclose any specificcompounds of the formula (II) or (III) or methods for the preparationthereof.

In particular, the regioselective introduction of the substituents Q orX to compounds of the formula (I) represents a major challenge. This ismade particularly difficult by the two chemically very similar ringsystems which are coupled to each other in the compounds of the formula(I). The metallation and subsequent halogenation on the pyridine ring ofsuch imidazopyridines has not been described to date in the literature.

Only synthetic methods for preparing uncoupled halogenated pyridinederivatives are known from the prior art. In addition, however, thesechemical synthetic methods that have been described in the prior art todate very frequently make use of methods that are not economicallyimplementable from an industrial point of view and/or have otherdisadvantages.

In the case of lithium bases and magnesium bases in particular,disadvantages are the low chemical yields, performing at very lowtemperatures and the difficult regio- and chemoselectivity of thedeprotonation due to the high reactivity of these reagents. Sometimes atransmetallation with zinc salts, such as zinc chloride for example, isnecessary in order to carry out further selective reactions such asNegishi cross couplings as described in Organic Letters 2008 (10), p.2497ff. The preparation is therefore very expensive (many salts areformed) and unsuitable for industrial scale commercial processes.

With regard to the disadvantages outlined above, there is an urgent needfor a simplified, industrially and economically performable method forpreparing halogenated imidazopyridine derivatives, especiallyhalogenated or substituted imidazopyridine derivatives of the formula(II) or (III). The halogenated imidazopyridine derivatives obtainable bythis method sought are preferably to be obtained with good yield, highpurity and in an economic manner.

It has been found, surprisingly, that halogenated imidazopyridinederivatives of the formula (II) can be prepared advantageously in amethod using an organozinc base, in particular even with high regio- andchemoselectivity and good yield.

The present invention accordingly provides a method for preparingcompounds of the formula (II)

in which (configuration 1)

-   Q and Z are each independently halogen,-   A¹ is nitrogen, ═N⁺—O⁻ or ═C—R⁵,-   A² is —N—R⁶, oxygen or sulfur,-   R¹ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, amino, (C₁-C₆)alkylamino,    di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,    (C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,    aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,    di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,    -   or is (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyl,        (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, each of which is optionally        mono- or polysubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl or heterocyclyl may each optionally be mono-        or polysubstituted by identical or different substituents from        the group consisting of halogen, cyano, nitro, hydroxyl, amino,        carboxy, carbamoyl, aminosulfonyl, (C₁-C₆)alkyl,        (C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkyl,        (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,        (C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkylsulfoximino, (C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)alkoxycarbonyl, (C₁-C₆)alkylcarbonyl,        (C₃-C₆)trialkylsilyl and benzyl,-   R³ is hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,    (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,    (C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,    (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl    ((C₁-C₆)alkylcarbonylamino), or    -   is aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and where possible substituents in each        case are as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl,        (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,        (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,        (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,        (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,        (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,        (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,        (C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,        (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl        or (C₃-C₈)cycloalkylamino,-   R⁴ is hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,    (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,    (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,    (C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,    (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl    ((C₁-C₆)alkylcarbonylamino), or    -   is aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and where possible substituents in each        case are as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,        (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl,        (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,        (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,        (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,        (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,        (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,        (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,        (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,        (C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,        (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,        (C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino,-   R⁵ is hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,    (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,    (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,    (C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,    (C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,    (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,    (C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,    (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,    (C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl    ((C₁-C₆)alkylcarbonylamino) and-   R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,    halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or    (C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl,    characterized in that, in a first method step a), a compound of the    formula (I)

in which Z, R¹, R³, R⁴, A¹ and A² are each as defined above,is reacted with an organozinc base of the structure(NR^(a)R^(b))—Zn—R^(c) or (NR^(a)R^(b))₂—Zn, in whichR^(c) is halogen or —O-pivaloyl andR^(a) and R^(b) together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂—group, where each of these groups may optionally be substituted by 1, 2,3 or 4 R^(d) radicals and R^(d) is selected from the group consisting ofmethyl, ethyl, n-propyl and isopropyl,to give a compound of the formula (IVa) or the formula (IVb),

in which Z, R¹, R³, R⁴, R^(c), A¹ and A² are each as defined above,and this compound of the formula (IVa) or (IVb) is reacted in a secondmethod step b) with a compound of the structure Q-V, in which V ishalogen and Q has the abovementioned definition, to give the compound ofthe formula (II).

The compound Q-V, as apparent from the definitions of Q and V, is aninterhalogen compound, preferably elemental halogen. Q and V need notnecessarily be the same halogen. For example, Q may be iodine or bromineand V may be chlorine, bromine or iodine. Preferably, the compound Q-V,however, is an elemental halogen, especially F₂, Cl₂, Br₂ or I₂.Particular preference is given to I₂ or Br₂, very particular preferenceto I₂.

The radicals Z and Q are preferably different halogens, Z particularlypreferably being fluorine, chlorine or bromine and in the case that

Z is fluorine, Q is iodine, bromine or chlorine orZ is chlorine, Q is iodine or bromine orZ is bromine, Q is iodine.

The compounds of the formula (IVa) and (IVb) may also be presentcomplexed with salts, where the salts are preferably alkali metalhalides or alkaline earth metal halides, preferably lithium chlorideand/or magnesium chloride and particularly preferably lithium chloride.

Preferred and particularly preferred definitions of the Q, Z, R¹, R³,R⁴, R^(c), A¹ and A² radicals included in the aforementioned formulae(I), (II), (IVa) and (IVb) of the method according to the invention areelucidated hereinafter, with more specific description of the organozincbase further down, and so the preferred configurations of the base arespecified at that point.

(Configuration 2)

-   Q is preferably chlorine, iodine or bromine,-   Z is preferably bromine, fluorine or chlorine,-   R^(c) is preferably —O-pivaloyl, chlorine, bromine or iodine,-   A¹ is preferably nitrogen, ═N⁺—O⁻ or ═C—R⁵,-   A² is preferably —N—R⁶ or oxygen,-   R¹ is preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    (C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonylamino,    -   or is (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl,        (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, each of which is optionally        mono- or disubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl or heterocyclyl may each optionally be mono-        or disubstituted by identical or different substituents from the        group consisting of halogen, cyano, carbamoyl, aminosulfonyl,        (C₁-C₄)alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)alkylsulfimino,-   R³ is preferably hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,    amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di(C₁-C₄)alkylaminosulfonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino) or    -   is phenyl or hetaryl, each of which is optionally mono- or        disubstituted by identical or different substituents, where (in        the case of hetaryl) at least one carbonyl group may optionally        be present and where possible substituents in each case are as        follows: cyano, halogen, nitro, acetyl, amino, (C₁-C₄)alkyl,        (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,        (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,        (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,        (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,        (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino,        di(C₁-C₄)alkylamino, aminosulfonyl, (C₁-C₄)alkylaminosulfonyl        and di(C₁-C₄)alkylaminosulfonyl,-   R⁴ is preferably hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,    amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di(C₁-C₄)alkylaminosulfonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),    -   is furthermore preferably phenyl or hetaryl, each of which is        optionally mono- or disubstituted by identical or different        substituents, where (in the case of hetaryl) at least one        carbonyl group may optionally be present and where possible        substituents in each case are as follows: cyano, halogen, nitro,        acetyl, amino, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,        (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkylhydroxyimino,        (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,        (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino,        di(C₁-C₄)alkylamino, aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,        di(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl        ((C₁-C₄)alkylcarbonylamino),-   R⁵ is preferably hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,    amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,    (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkylhydroxyimino,    (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di(C₁-C₄)alkylaminosulfonyl, aminothiocarbonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino) and-   R⁶ is preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)haloalkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkylthio-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl.

(Configuration 3)

-   Q is particularly preferably chlorine, iodine or bromine,-   Z is particularly preferably bromine, fluorine or chlorine,-   R^(c) is particularly preferably —O-pivaloyl, chlorine, bromine or    iodine,-   A¹ is particularly preferably nitrogen or ═C—R⁵,-   A² is particularly preferably —N—R⁶,-   R¹ is particularly preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,-   R³ is particularly preferably hydrogen, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio,    (C₁-C₄)haloalkylsulfinyl or (C₁-C₄)haloalkylsulfonyl,-   R⁴ is particularly preferably hydrogen, cyano, halogen, nitro,    hydroxyl, amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    cyano(C₃-C₈)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,    (C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,    (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),    -   is furthermore particularly preferably phenyl or hetaryl, each        of which is optionally mono- or disubstituted by identical or        different substituents, where (in the case of hetaryl) at least        one carbonyl group may optionally be present and where possible        substituents in each case are as follows: cyano, halogen,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,        (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylhydroxyimino,        (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino,        di(C₁-C₄)alkylamino, aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,        di(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl        ((C₁-C₄)alkylcarbonylamino),-   R⁵ is particularly preferably hydrogen, halogen, cyano or    (C₁-C₄)alkyl and-   R⁶ is particularly preferably (C₁-C₄)alkyl or    (C₁-C₄)alkoxy-(C₁-C₄)alkyl.

(Configuration 4)

-   Q is especially preferably iodine or bromine,-   Z is especially preferably bromine or chlorine,-   R^(c) is especially preferably chlorine, bromine or iodine,-   A¹ is especially preferably nitrogen or ═C—R⁵,-   A² is especially preferably —N—R⁶,-   R¹ is especially preferably methyl, ethyl, n-propyl, isopropyl,    cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R³ is especially preferably fluorine, chlorine, fluoromethyl,    difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,    trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulfonyl or    trifluoromethylsulfinyl,-   R⁴ is especially preferably hydrogen, cyano, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl or    NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino),-   R⁵ is especially preferably hydrogen, fluorine, chlorine, bromine or    cyano and-   R⁶ is especially preferably methyl, ethyl, isopropyl, methoxymethyl    or methoxyethyl.

(Configuration 5)

-   Q is particularly iodine or bromine,-   Z is particularly bromine or chlorine,-   R^(c) is particularly chlorine or bromine,-   A¹ is particularly nitrogen,-   A² is particularly —N—R⁶,-   R¹ is particularly methyl, ethyl, n-propyl, isopropyl or    cyclopropyl,-   R³ is particularly trifluoromethyl or pentafluoroethyl,-   R⁴ is particularly hydrogen and-   R⁶ is particularly methyl.

(Configuration 6)

-   Q is especially iodine or bromine,-   Z is especially bromine or chlorine,-   R^(c) is especially chlorine,-   A¹ is especially nitrogen,-   A² is especially —N—R⁶,-   R¹ is especially ethyl,-   R³ is especially trifluoromethyl,-   R⁴ is especially hydrogen and-   R⁶ is especially methyl.

The radical definitions and elucidations given above apply both to theend products and intermediates and to the starting materials in acorresponding manner. These radical definitions can be combined with oneanother as desired, i.e. including combinations between the respectivepreferred ranges.

By definition, unless stated otherwise, halogen is selected from thegroup of fluorine, chlorine, bromine and iodine, preferably in turn fromthe group of fluorine, chlorine and bromine.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated, aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. The alkynyl radical may also contain at leastone double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

According to the invention, unless defined differently elsewhere, theterm “aryl” is understood to mean an aromatic radical having 6 to 14carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthrenyl,more preferably phenyl.

Unless defined differently elsewhere, the term “arylalkyl” is understoodto mean a combination of the radicals “aryl” and “alkyl” defined inaccordance with the invention, where the radical is generally bonded viathe alkyl group; examples of these are benzyl, phenylethyl orα-methylbenzyl, particular preference being given to benzyl.

Unless defined differently elsewhere, “hetaryl” or “heteroaromatic ring”denotes a mono-, bi- or tricyclic heterocyclic group composed of carbonatoms and at least one heteroatom, where at least one ring is aromatic.Preferably, the hetaryl group contains 3, 4, 5, 6, 7 or 8 carbon atoms.Particular preference is given here to monocyclic groups of 3, 4, 5, 6,7 or 8 carbon atoms and at least one heteroatom. The hetaryl group isparticularly preferably selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl,1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl,1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl,1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl,benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl,indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl,benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl,isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, imidazopyridinyland indolizinyl.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Unless stated otherwise, optionally substituted radicals maybe mono- or polysubstituted, where the substituents in the case ofpolysubstitutions may be the same or different.

Advantageously, the halogenated imidazopyridine derivatives of theformula (II) can be prepared by the method according to the inventionwith good yields and in high purity. Because of the very good functionalgroup tolerance of zinc reagents, zinc bases are very attractive. Regio-and chemoselective metallations of imidazopyridines in the presence ofstoichiometric amounts of selective bases are made possible, even atelevated temperatures, without aryne elimination taking place orsensitive functional groups being attacked. The zinc compound formed asintermediate can subsequently be scavenged with various electrophiles,as described by way of example in Organic Letters 2009 (11), p. 1837ff.These imidazopyridine derivatives having novel substitution can then befurther reacted as valuable synthons.

The method according to the invention can be elucidated by the followingscheme (I):

In this scheme, Q, V, Z, R¹, R³, R⁴, R^(c), A¹ and A² are as definedabove. The compounds shown in brackets are the intermediate (formula(IVa) or formula (IVb)) which is reacted further to give the compound ofthe formula (II). Accordingly, the method according to the invention canbe divided into the two method steps a) and b), step a) being theconversion of the compound of the formula (I) to the respectiveintermediate and step b) being the further conversion of theintermediate to the compound of the formula (II).

General Definitions

In the context of the present invention, the term halogen, unlessdefined otherwise, encompasses those elements selected from the groupconsisting of fluorine, chlorine, bromine and iodine.

The term “halides” in connection with the present invention describescompounds between halogens and elements of other groups of the PeriodicTable, which can give rise to halide salts (ionic compounds (salts)which consist of anions and cations because of the great difference inelectronegativity between the elements involved and are held together byelectrostatic interactions) or covalent halides (covalent compoundswhere the difference in electronegativity is not as great as in theaforementioned ionic compounds, but the bonds have charge polarity),depending on the nature of the chemical bond. Particular preference isgiven in accordance with the invention to halide salts.

The term “pivaloyl” in the context of the present invention describesthe deprotonated radical of pivalic acid (IX) having the empiricalformula (CH₃)₃CCO₂H.

“O-pivaloyl” correspondingly means that the bond of the pivaloyl radicalis via the deprotonated oxygen atom of the acid group.

Optionally substituted groups may be mono- or polysubstituted, where thesubstituents in the case of polysubstitutions may be the same ordifferent.

Alkyl groups substituted by one or more halogen atoms (-Hal) are, forexample, selected from trifluoromethyl (CF₃), difluoromethyl (CHF₂),CF₃CH₂, ClCH₂ or CF₃CCl₂.

Alkyl groups in the context of the present invention, unless definedotherwise, are straight-chain, branched or cyclic saturated hydrocarbylgroups.

The definition C₁-C₁₂-alkyl encompasses the widest range defined hereinfor an alkyl group. Specifically, this definition encompasses, forexample, the meanings of methyl, ethyl, n-, isopropyl, n-, iso-, sec-and t-butyl, n-pentyl, n-hexyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl,n-heptyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.

The conversion of the compounds of the formula (I) to compounds of theformula (IVa) or formula (IVb) in the first method step (step a)) iseffected in the presence of an organozinc base of the structure(NR^(a)R^(b))—Zn—R^(c) or (NR^(a)R^(b))₂—Zn, in which (configurationB-1)

R^(c) is as defined above (configuration 1) (and is therefore halogen or—O-pivaloyl),R^(a) and R^(b) together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂—group, where each of these groups may optionally be substituted by 1, 2,3 or 4 R^(d) radicals andR^(d) is selected from the group consisting of methyl, ethyl, n-propyland isopropyl.

It is preferable that (configuration B-2)

R^(c) is as defined above as preferred (configuration 2) (and istherefore —O-pivaloyl, chlorine, bromine or iodine),R^(a) and R^(b) together form a —(CH₂)— group, where each of thesegroups may optionally be substituted by 1, 2, 3 or 4 R^(d) radicals andR^(d) is selected from the group consisting of methyl and ethyl.

It is particularly preferable that (configuration B-3)

R^(c) is as defined above as particularly preferred (configuration 6)(and is therefore chlorine) andR^(a) and R^(b) together form a —(CH₂)₅— group substituted by 4 methylgroups.

The radical definitions given above can be combined with one another asdesired, i.e. including combinations between the respective preferredranges.

In a very particularly preferred configuration of the base according tothe invention, the structural element (NR^(a)R^(b)) istetramethylpiperidine (TMP) of formula (V).

Organozinc bases most preferred in accordance with the invention areaccordingly characterized in that zinc is bound to TMP, especially inthe form of zinc halide and most preferably in the form of zincchloride. Bases of this kind have the following structure of the formula(VI) (configuration B-4)

(TMP)_(x)ZnCl_(2-x),  (VI)

in which x is the number 1 or 2. Among these, preference is given inturn to bases with x=1 (configuration B-5) of formula (VII):

In a further preferred embodiment of the method according to theinvention, the organometallic base is present in conjunction with alkalimetal halides or alkaline earth metal halides. This is especially trueof bases of the formulae (VI) and (VII). Particularly preferred alkalimetal halides or alkaline earth metal halides of this kind are lithiumchloride and magnesium chloride, very particular preference being givento lithium chloride. Organometallic bases that are very particularlypreferred in accordance with the invention are accordingly TMP ZnCl.LiClor (TMP)₂Zn.2LiCl or (TMP)₂Zn.2LiCl 2 MgCl₂ (configuration B-6). Mostpreferred is TMP ZnCl.LiCl (VIII; configuration B-7).

Specific combinations of compounds of the formulae (I), (II) and (IVa)or (IVb) with bases according to the invention are cited hereinafter byway of example in Table 1, these being employable in a method accordingto the invention. Since, in some configurations, the structural elementR is present both in the base according to the invention and in thecompound of the formula (IVa), the narrowest definition applies to R^(c)in each case.

TABLE 1 Compounds of the formulae (I), (II) Number and (IVa) or (IVb)Base according to 1 Configuration 1 Configuration B-1 2 Configuration 1Configuration B-2 3 Configuration 1 Configuration B-3 4 Configuration 1Configuration B-4 5 Configuration 1 Configuration B-5 6 Configuration 1Configuration B-6 7 Configuration 1 Configuration B-7 8 Configuration 2Configuration B-1 9 Configuration 2 Configuration B-2 10 Configuration 2Configuration B-3 11 Configuration 2 Configuration B-4 12 Configuration2 Configuration B-5 13 Configuration 2 Configuration B-6 14Configuration 2 Configuration B-7 15 Configuration 3 Configuration B-116 Configuration 3 Configuration B-2 17 Configuration 3 ConfigurationB-3 18 Configuration 3 Configuration B-4 19 Configuration 3Configuration B-5 20 Configuration 3 Configuration B-6 21 Configuration3 Configuration B-7 22 Configuration 4 Configuration B-1 23Configuration 4 Configuration B-2 24 Configuration 4 Configuration B-325 Configuration 4 Configuration B-4 26 Configuration 4 ConfigurationB-5 27 Configuration 4 Configuration B-6 28 Configuration 4Configuration B-7 29 Configuration 5 Configuration B-1 30 Configuration5 Configuration B-2 31 Configuration 5 Configuration B-3 32Configuration 5 Configuration B-4 33 Configuration 5 Configuration B-534 Configuration 5 Configuration B-6 35 Configuration 5 ConfigurationB-7 36 Configuration 6 Configuration B-1 37 Configuration 6Configuration B-2 38 Configuration 6 Configuration B-3 39 Configuration6 Configuration B-4 40 Configuration 6 Configuration B-5 41Configuration 6 Configuration B-6 42 Configuration 6 Configuration B-7

Preferably, the organometallic base is used in the method according tothe invention in a total amount of 0.5 to 5 equivalents, preferably of0.8 to 2 equivalents, further preferably of 1 to 1.5 equivalents andmore preferably of 1.0 to 1.2 equivalents, based on the compound of theformula (I). One advantage of the method according to the invention inthis regard is that the organometallic base can be used in virtuallystoichiometric amounts.

Depending on whether the structural element (NR^(a)R^(b)) is presentonce or twice in the organozinc base used, intermediate compounds of theformula (IVa) or of the formula (IVb) are formed in method step a).

The conversion of the compounds of the formula (IVa) or (IVb) tocompounds of the formula (II) in the second method step (step b)) iseffected in the presence of a compound Q-V in which Q and V each havethe definitions given above. Since both Q and V are halogen, thecompound is an interhalogen compound. Q and V need not necessarily bethe same halogen. For example, Q may be iodine or bromine and V may bechlorine, bromine or iodine. Preferably, the compound Q-V, however, isan elemental halogen, especially F₂, Cl₂, Br₂ or I₂. Particularpreference is given to I₂ or Br₂, very particular preference to I₂.

Q-V is preferably selected such that the radicals Z and Q are differenthalogens, particularly preferably in the case that

Z is fluorine, Q is iodine, bromine or chlorine orZ is chlorine, Q is iodine or bromine orZ is bromine, Q is iodine.

Preferably, the compound Q-V is used in the method according to theinvention in a total amount of 0.5 to 10.0 equivalents, preferably of0.8 to 5 equivalents, further preferably of 1 to 2.5 equivalents andmore preferably of 1.0 to 1.5 equivalents, based on the compound of theformula (I).

The conversion according to the invention of the compounds of theformula (I) to compounds of the formula (IVa) or (IVb) and further tocompounds of the formula (II) is preferably effected in the presence ofan organic solvent in each case. Useful solvents in principle includeall organic solvents which are inert under the reaction conditionsemployed and in which the compounds to be converted have adequatesolubility. Suitable solvents especially include: tetrahydrofuran (THF),1,4-dioxane, diethyl ether, diglyme, methyl tert-butyl ether (MTBE),tert-amyl methyl ether (TAME), 2-methyl-THF, toluene, xylenes,mesitylene, ethylene carbonate, propylene carbonate,N,N-dimethylacetamide, N,N-dimethylformamide (DMF), N-methylpyrrolidone(NMP), N-ethyl-2-pyrrolidone (NEP), N-butyl-2-pyrrolidone (NBP);N,N′-dimethylpropyleneurea (DMPU), halohydrocarbons and aromatichydrocarbons, especially chlorohydrocarbons such as tetrachloroethylene,tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane,chloroform, carbon tetrachloride, trichloroethane, trichloroethylene,pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene,bromobenzene, dichlorobenzene, especially 1,2-dichlorobenzene,chlorotoluene, trichlorobenzene; 4-methoxybenzene, fluorinatedaliphatics and aromatics, such as trichlorotrifluoroethane,benzotrifluoride and 4-chlorobenzotrifluoride. It is also possible touse solvent mixtures, preferably mixtures of the solvents mentionedabove such as tetrahydrofuran (THF), 1,4-dioxane, diethyl ether,diglyme, methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene, xylenes, mesitylene, dimethylformamide (DMF).

Preferred solvents are THF, N,N-dimethylformamide (DMF), 1,4-dioxane,diglyme, methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene and 4-methoxybenzene.

Particularly preferred solvents are THF and N,N-dimethylformamide (DMF),very particular preference being given to THF.

The solvent may also be degassed (oxygen-free).

Preference is given to using the same solvent for both method steps a)and b). Alternative configurations of the invention in which differentsolvents are used for method steps a) and b) are likewise possible,however, in which case the solvents are likewise preferably selectedfrom the aforementioned solvents, and the respective solvents specifiedas being preferred, particularly preferred and especially preferred areapplicable to the respective method step a) or b).

The reaction of method step a) is particularly good at elevatedtemperatures. The reaction in method step a) is therefore generallyconducted at a temperature between 0° C. and 110° C. and with increasingpreference between 20° C. and 100° C., between 30° C. and 95° C.,between 40° C. and 90° C., between 60° C. and 85° C., and mostpreferably between 70° C. and 85° C., for example at 80° C.

The reaction in method step b) is generally conducted at a temperaturebetween 0° C. and 80° C. and with increasing preference between 10° C.and 70° C., between 15° C. and 60° C., between 20° C. and 50° C.,between 20° C. and 40° C., and most preferably between 20° C. and 35°C., for example at room temperature or 25° C.

The reaction is typically conducted at standard pressure, but can alsobe conducted at elevated or reduced pressure.

The desired compounds of the formula (II) can be isolated, for example,by aqueous workup in the presence of saturated ammonium chloride orsodium thiosulfate solutions and/or subsequent chromatography. Suchmethods are known to those skilled in the art and also includecrystallization from an organic solvent or solvent mixture.

A particularly preferred embodiment of the method according to theinvention can be elucidated with reference to the following scheme (II):

In this scheme, Q, V, Z, R¹, R³, R⁴, A¹ and A² are as defined above. Thecompound shown in brackets represents the corresponding intermediate ofthe formula (IVa) which is further reacted to give the product, acompound of the formula (II). Both reactions take place in THF assolvent. “Equiv” refers to the amount of equivalents of TMPZnCl.LiCl oriodine (I₂) used.

In a specific embodiment of the invention, the compounds of the formula(II) are reacted further in a third step c) to give compounds of theformula (III)

in which Z, R¹, R³, R⁴, A¹ and A² have the abovementioned definitionsand preferred ranges according to any of configurations 1 to 6 and

(Configuration (X-1))

-   X is cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,    (C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkoxyimino,    —N═C(H)—O(C₁-C₆)alkyl, —C(H)═N—O(C₁-C₆)alkyl,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,    (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,    (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, (C₂-C₆)alkenylaminocarbonyl,    di(C₂-C₆)alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,    (C₁-C₆)alkylsulfonylamino, (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,    aminosulfonyl, (C₁-C₆)alkylaminosulfonyl,    di(C₁-C₆)alkylaminosulfonyl, (C₁-C₆)alkylsulfoximino,    aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino,    (C₁-C₆)alkylcarbamoyl (including —NHCOO(C₁-C₆)alkyl,    —N(C₁-C₆)alkylCOO(C₁-C₆)alkyl, —OCONH(C₁-C₆)alkyl or    —OCON(C₁-C₆)dialkyl), (C₁-C₆)alkylcarbonylamino ((C₁-C₆)alkylCONH),    (C₁-C₆)alkylurea (including —NHCONH(C₁-C₆)alkyl, and    —NHCON(C₁-C₆)dialkyl) or is a saturated, partially saturated or    heteroaromatic ring which is optionally mono- or polysubstituted by    identical or different substituents and in which at least one carbon    atom is replaced by a heteroatom, or is an aromatic ring which is    mono- or polysubstituted by identical or different substituents,    where at least one carbonyl group may optionally be present in each    case and where possible substituents in each case are as follows:    cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,    (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,    hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,    (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,    (C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,    (C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,    (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkoxyimino,    —N═C(H)—O(C₁-C₆)alkyl, —C(H)═N—O(C₁-C₆)alkyl,    (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,    (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,    (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,    (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,    (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,    (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)alkylaminocarbonyl,    di(C₁-C₆)alkylaminocarbonyl, (C₂-C₆)alkenylaminocarbonyl,    di(C₂-C₆)alkenylaminocarbonyl, (C₃-C₈)cycloalkylaminocarbonyl,    (C₁-C₆)alkylsulfonylamino, (C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,    aminosulfonyl, (C₁-C₆)alkylaminosulfonyl,    di(C₁-C₆)alkylaminosulfonyl, (C₁-C₆)alkylsulfoximino,    aminothiocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,    di(C₁-C₆)alkylaminothiocarbonyl, (C₃-C₈)cycloalkylamino or    (C₁-C₆)alkylcarbonylamino.

Preference is given to compounds of the formula (III) in which Z, R¹,R³, R⁴, A¹ and A² have the abovementioned definitions and preferredranges according to any of configurations 1 to 6 and

(Configuration (X-2))

-   X is preferably cyano, halogen, nitro, acetyl, amino, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,    (C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkoxyimino,    —N═C(H)—O(C₁-C₄)alkyl, —C(H)═N—O(C₁-C₄)alkyl,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,    di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,    (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulfonyl,    (C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,    (C₁-C₄)alkylcarbamoyl (including —NHCOO(C₁-C₄)alkyl,    —N(C₁-C₄)alkylCOO(C₁-C₄)alkyl, —OCONH(C₁-C₄)alkyl or    —OCON(C₁-C₄)dialkyl), (C₁-C₄)alkylcarbonylamino ((C₁-C₄)alkylCONH)    or (C₁-C₄)alkylurea (including —NHCONH(C₁-C₆)alkyl and    —NHCON(C₁-C₆)dialkyl).

Particular preference is given to compounds of the formula (III) inwhich Z, R, R³, R⁴, A¹ and A² have the abovementioned definitions andpreferred ranges according to any of configurations 1 to 6 and

(Configuration (X-3))

-   X is cyano, halogen, nitro, acetyl, amino, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,    (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,    (C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)cyanoalkoxy or (C₁-C₄)alkoxy-(C₁-C₄)alkoxy.

Very particular preference is given to compounds of the formula (III) inwhich Z, R, R³, R⁴, A and A² have the abovementioned definitions andpreferred ranges according to any of configurations 1 to 6 and

(Configuration (X-4))

-   X is cyano, halogen, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, ((C₁-C₄)alkoxy or    (C₁-C₄)cyanoalkoxy.

Emphasis is given to compounds of the formula (III) in which Z, R¹, R³,R⁴, A¹ and A² have the abovementioned definitions and preferred rangesaccording to any of configurations 1 to 6 and

(Configuration (X-5-1))

-   X is cyano, halogen, (C₁-C₄)alkyl, (C₃-C₆)cycloalkyl,    (C₂-C₄)alkynyl, (C₂-C₄)alkenyl, (C₃-C₆)cyanocycloalkyl or    (C₃-C₆)halocycloalkyl.

Emphasis is further given to compounds of the formula (III) in which Z,R¹, R³, R⁴, A¹ and A² have the abovementioned definitions and preferredranges according to any of configurations 1 to 6 and

(Configuration (X-5-2))

-   X is cyano, halogen, (C₁-C₄)alkyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cyanocycloalkyl or (C₃-C₆)halocycloalkyl.

Particular preference is given to compounds of the formula (III) inwhich Z, R, R³, R⁴, A¹ and A² have the abovementioned definitions andpreferred ranges according to any of configurations 1 to 6 and

(Configuration (X-6-1))

-   X is cyano, methyl, ethyl, vinyl, ethynyl or chlorine.

Particular preference is further given to compounds of the formula (III)in which Z, R¹, R³, R⁴, A¹ and A² have the abovementioned definitionsand preferred ranges according to any of configurations 1 to 6 and

(Configuration (X-6-2))

-   X is cyano, methyl or chlorine.

The conversion of the compounds of the formula (II) to compounds of theformula (III) (step c), i.e. the introduction of the radical X, ispreferably carried out by coupling, particularly preferably by across-coupling or a metal-catalysed reaction.

The compounds of the formula (II) are reacted in this case preferablywith organozinc reagents in the presence of a catalyst or with metalsalts, particularly copper salts.

Reactions of this kind are described, for example, in Chemistry, AEuropean Journal 15 (2009) (organozinc reagents) and Organic Letters, 13(2011), 648-651 or Organic & Biomolecular Chemistry, 7 (2009), 1043-1052(metal salts).

The conversion according to the invention of the compounds of theformula (II) to compounds of the formula (III) is preferably effected inthe presence of an organic solvent in each case. Useful solvents inprinciple include all organic solvents which are inert under thereaction conditions employed and in which the compounds to be convertedhave adequate solubility. The solvent may also be degassed(oxygen-free).

Preferably, the organozinc compound or the metal salt in the methodaccording to the invention is used in a total amount of 0.5 to 10equivalents, preferably 0.8 to 5 equivalents, particularly preferably 1to 3.0 equivalents, based on the compound of the formula (II).

The reaction in method step c) is generally conducted at a temperaturebetween 0° C. and 110° C. and with increasing preference between 10° C.and 100° C., between 20° C. and 90° C., and most preferably between 30°C. and 90° C.

The reaction is typically conducted at standard pressure, but can alsobe conducted at elevated or reduced pressure.

Introduction of the Radical X Via Organozinc Reagents:

The compounds of the formula (III) can be prepared by Negishicross-coupling using organozinc reagents in the presence of a catalyst,as described in Chemistry, A European Journal 15 (2009), 1468-1477.

Preferably, the organozinc compound is used in the method according tothe invention in a total amount of 0.5 to 10 equivalents, preferably of0.8 to 5 equivalents, further preferably of 1.0 to 3.5 equivalents andmore preferably of 1.5 to 3.0 equivalents, based on the compound of theformula (II). An advantage of the method according to the invention inthis regard is that the organozinc reagent is commercially available andmay be used in a highly regio- and chemoselective manner.

Preferred zinc reagents are those of the formula YZnCl or YZnBr,particular preference being given to YZnCl, where

Configuration (Y-1)

-   Y is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, ((C₁-C₄)alkyl-(C₃-C₆)cycloalkyl    and the reagents may also be present complexed with lithium chloride    and/or magnesium chloride.

With particular preference (configuration Y-2)

-   Y is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl or    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl.

With very particular preference (configuration Y-3), Y is (C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkynyl or (C₃-C₆)cycloalkyl.

In particular (configuration Y-4), Y is methyl, ethyl, propyl, butyl,vinyl, ethynyl or cyclopropyl.

The reaction with organozinc reagents in method step c) is furtherpreferably carried out in the presence of a catalyst. Preferably, thecatalyst is a palladium compound or a nickel compound. More preferably,the catalyst is a palladium compound. It is especially preferablytetrakis(triphenylphosphine)palladium(0), abbreviated to Pd(PPh₃)₄, ofthe formula (XI).

In the reaction with organozinc reagents in step c), 2.5 to 25 mol % andpreferably 5 to 20 mol % catalyst is typically used.

The conversion according to the invention of the compounds of theformula (II) to compounds of the formula (III) using organozinc reagentsis preferably effected in the presence of an organic solvent in eachcase. Suitable solvents especially include: tetrahydrofuran (THF),1,4-dioxane, diethyl ether, diglyme, methyl tert-butyl ether (MTBE),tert-amyl methyl ether (TAME), 2-methyl-THF, toluene, xylenes,mesitylene, ethylene carbonate, propylene carbonate,N,N-dimethylacetamide, N,N-dimethylformamide (DMF), N-methylpyrrolidone(NMP), N-ethyl-2-pyrrolidone (NEP), N-butyl-2-pyrrolidone (NBP);N,N′-dimethylpropyleneurea (DMPU), halohydrocarbons and aromatichydrocarbons, especially chlorohydrocarbons such as tetrachloroethylene,tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane,chloroform, carbon tetrachloride, trichloroethane, trichloroethylene,pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene,bromobenzene, dichlorobenzene, especially 1,2-dichlorobenzene,chlorotoluene, trichlorobenzene; 4-methoxybenzene, fluorinatedaliphatics and aromatics, such as trichlorotrifluoroethane,benzotrifluoride and 4-chlorobenzotrifluoride. It is also possible touse solvent mixtures, preferably mixtures of the aforementioned solventssuch as tetrahydrofuran (THF), 1,4-dioxane, diethyl ether, diglyme,methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene, xylenes, mesitylene, dimethylformamide (DMF).

Preferred solvents are THF, N,N-dimethylformamide (DMF), 1,4-dioxane,diglyme, methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene and 4-methoxybenzene.

Particularly preferred solvents are THF and N,N-dimethylformamide (DMF),very particular preference being given to THF.

The reaction with organozinc reagents in method step c) is generallyconducted at a temperature between 0° C. and 80° C. and with increasingpreference between 5° C. and 75° C., between 10° C. and 70° C., between20° C. and 60° C., between 25° C. and 65° C., and most preferablybetween 30° C. and 50° C., for example at 40° C.

The reaction with organozinc reagents in method step c) is generallycarried out with a reaction time of between 0.5 and 10 h and withincreasing preference of between 1 and 7 h, between 1.5 and 6 h andespecially preferably between 2 and 5 h, for example 3 h. The desiredcompounds of the formula (III) can be isolated, for example, by aqueousworkup in the presence of saturated ammonium chloride or sodiumthiosulfate solutions and/or subsequent chromatography. Such processesare known to those skilled in the art and also include crystallizationfrom an organic solvent or solvent mixture.

Introduction of the Radical X Via Metal Salts:

The compounds of the formula (III) can be prepared by Negishicross-coupling using metal salts, as described in Organic Letters, 13(2011), 648-651 or Organic & Biomolecular Chemistry, 7 (2009),1043-1052.

Preferably, the metal salts are used in the method according to theinvention in a total amount of 0.5 to 10 equivalents, preferably of 0.8to 5 equivalents, further preferably of 1 to 2.5 equivalents and morepreferably of 1.0 to 1.5 equivalents, based on the compound of theformula (II). An advantage of the method according to the invention inthis regard is that the metal salts are commercially available and maybe used in a highly regio- and chemoselective manner. In addition, theaddition of a catalyst may be omitted.

Preferred metal salts are copper salts and particular preference isgiven to CuCN or CuCl.

The conversion according to the invention of the compounds of theformula (II) to compounds of the formula (III) using metal salts ispreferably effected in the presence of an organic solvent in each case.Suitable solvents especially include: pyridine, tetrahydrofuran (THF),1,4-dioxane, diethyl ether, diglyme, methyl tert-butyl ether (MTBE),tert-amyl methyl ether (TAME), 2-methyl-THF, toluene, xylenes,mesitylene, ethylene carbonate, propylene carbonate,N,N-dimethylacetamide, N,N-dimethylformamide (DMF), N-methylpyrrolidone(NMP), N-ethyl-2-pyrrolidone (NEP), N-butyl-2-pyrrolidone (NBP);N,N′-dimethylpropyleneurea (DMPU), halohydrocarbons and aromatichydrocarbons, especially chlorohydrocarbons such as tetrachloroethylene,tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane,chloroform, carbon tetrachloride, trichloroethane, trichloroethylene,pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene,bromobenzene, dichlorobenzene, especially 1,2-dichlorobenzene,chlorotoluene, trichlorobenzene; 4-methoxybenzene, fluorinatedaliphatics and aromatics, such as trichlorotrifluoroethane,benzotrifluoride and 4-chlorobenzotrifluoride. It is also possible touse solvent mixtures, preferably mixtures of the aforementioned solventssuch as tetrahydrofuran (THF), 1,4-dioxane, diethyl ether, diglyme,methyl tert-butyl ether (MTBE), tert-amyl methyl ether (TAME),2-methyl-THF, toluene, xylenes, mesitylene, dimethylformamide (DMF).

Preferred solvents are pyridine, THF, dioxane and DMF.

Particularly preferred solvents are pyridine, THF and DMF, veryparticular preference being given to pyridine.

The reaction with metal salts in method step c) is generally conductedat a temperature between 0° C. and 120° C. and with increasingpreference between 30° C. and 110° C., between 40° C. and 100° C.,between 50° C. and 90° C., between 60° C. and 95° C., and mostpreferably between 70° C. and 90° C., for example at 80° C.

The reaction with metal salts in method step c) is generally carried outwith a reaction time of between 1 and 8 and with increasing preferenceof between 2 and 7, between 2.5 and 7.5 and especially preferablybetween 3 h and 6 h, for example 5 h. The desired compounds of theformula (III) can be isolated, for example, by aqueous workup in thepresence of saturated ammonium chloride or sodium thiosulfate solutionsand/or subsequent chromatography. Such processes are known to thoseskilled in the art and also include crystallization from an organicsolvent or solvent mixture.

The present invention further provides compounds of the formula (IVa)

in which Z, R¹, R³, R⁴, R^(c), A¹ and A² have the abovementioneddefinitions and preferred configurations according to any ofconfigurations 1 to 6.

The compounds of the formula (IVa) may also be present complexed withsalts, where the salts are preferably alkali metal halides or alkalineearth metal halides, preferably lithium chloride and/or magnesiumchloride and particularly preferably lithium chloride.

Among the compounds of the formula (IVa), the following compounds areespecially preferred, in which the respective compound can be presentalone or as a lithium chloride complex:

The present invention further provides compounds of the formula (IVb)

in which Z, R¹, R³, R⁴, A¹ and A² have the abovementioned definitionsand preferred configurations.

The compounds of the formula (IVb) may also be present complexed withsalts, where the salts are preferably alkali metal halides or alkalineearth metal halides, preferably lithium chloride and/or magnesiumchloride as in structure (IVb-1) or (IVb-2) and particularly preferablylithium chloride (structure (IVb-1).

Z, R¹, R³, R⁴, A¹ and A² in formula (IVb-1) and (IVb-2) have theabovementioned definitions and preferred configurations.

The present invention further provides compounds of the formula (II)

in whichQ, Z, R¹, R³, R⁴, A¹ and A² have the abovementioned definitions andpreferred configurations.

Among the compounds of the formula (II), the following compounds areespecially preferred:

-   ((II-1),    2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine)

-   ((II-2),    2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine)

From these compounds of the formulae (II-1) to (II-2) arise theaccompanying reactants (I-1 to I-2) of the formula (I) of the methodaccording to the invention, which in each case are especially preferredcompounds of the formula (I).

The present invention further provides compounds of the formula (III)

in which Z, R¹, R³, R⁴, A¹ and A² have the abovementioned definitionsand preferred configurations according to any of configurations 1 to 6and X is as defined above according to any of configurations X-1 to X-6.

Among the compounds of the formula (III), the following compounds areespecially preferred:

-   ((III-1),    2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine)

-   ((III-2),    2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine)

-   ((III-3),    2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile)

-   ((III-4),    2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile)

-   ((III-5),    2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-chloro-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine)

The present invention is elucidated in more detail by the examples whichfollow, although the examples should not be interpreted in such a mannerthat they restrict the invention.

Methods:

The log P values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C 18). Temperature: 55° C.

The LC-MS determination in the acidic range is carried out at pH 2.7using the mobile phases 0.1% aqueous formic acid and acetonitrile(contains 0.1% formic acid); linear gradient from 10% acetonitrile to95% acetonitrile.

The LC-MS determination in the neutral range is carried out at pH 7.8using the mobile phases 0.001 molar aqueous ammonium bicarbonatesolution and acetonitrile; linear gradient from 10% acetonitrile to 95%acetonitrile.

Calibration is carried out using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data of selected examples are stated in classic form (values,multiplet splitting, number of hydrogen atoms).

In each case, the solvent in which the NMR spectrum was recorded isstated.

EXAMPLE 1 Synthesis of2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

2-[6-Chloro-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(628 mg, 1.42 mmol) in anhydrous THF (3 ml) was initially charged in adry, argon-filled 25-ml Schlenk flask, equipped with a magnetic stirrerbar and a septum. Zinc chloride-2,2,6,6-tetramethylpiperidin-1-idelithium chloride complex (TMPZnCl.LiCl) (1.31M in THF, 1.2 ml, 1.56mmol) was added dropwise and the mixture was stirred at 80° C. for 30minutes. The reaction mixture was cooled to 25° C., then iodine (507 mg,1.99 mmol) was added and the mixture was subsequently stirred at 25° C.for 30 minutes. Saturated aqueous ammonium chloride solution (25 ml) andsodium thiosulfate solution (25 ml) were added to the reaction mixturewhich was extracted with ethyl acetate (3*50 ml) and dried overanhydrous sodium sulfate. Following filtration, the solvent was removedunder reduced pressure. The crude product was purified bychromatography, which gave2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(464 mg, 61%) as a white solid.

HPLC-MS: log P=4.17; Mass (m/z): 499; ¹H-NMR (d₆-DMSO): δ 8.32 (s, 1H),8.16 (d, 1H), 7.80 (d, 1H), 4.06 (s, 3H), 3.05 (q, 2H), 1.20 (t, 3H).

EXAMPLE 2

Synthesis of2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

2-[6-Bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(500 mg, 1.19 mmol) in anhydrous THF (3 ml) was initially charged in adry, argon-filled 25-ml Schlenk flask, equipped with a magnetic stirrerbar and a septum. Zinc chloride-2,2,6,6-tetramethylpiperidin-1-idelithium chloride complex (TMPZnCl.LiCl) (1.31M in THF, 1.0 ml, 1.31mmol) was added dropwise and the mixture was stirred at 80° C. for 30minutes. The reaction mixture was cooled to 25° C., then iodine (426 mg,1.67 mmol) was added and the mixture was subsequently stirred at 25° C.for 30 minutes. Saturated aqueous ammonium chloride solution (25 ml) andsodium thiosulfate solution (25 ml) were added to the reaction mixturewhich was extracted with ethyl acetate (3*50 ml) and dried overanhydrous sodium sulfate. Following filtration, the solvent was removedunder reduced pressure. The crude product was purified bychromatography, which gave2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(302 mg, 82%) as a white solid.

HPLC-MS: log P=4.34; Mass (m/z): 543; ¹H-NMR (d₆-DMSO): δ 8.32 (s, 1H),8.04 (d, 1H), 7.90 (d, 1H), 4.06 (s, 3H), 3.04 (q, 2H), 1.20 (t, 3H).

EXAMPLE 3 (STEP C)

Synthesis of2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(700 mg, 1.4 mmol), dissolved in THF (4 ml), was added MeZnCl (2.0 M inTHF, 1.41 ml, 2.8 mmol) in the presence oftetrakis(triphenylphosphine)palladium(0) (163 mg, 0.14 mmol) at 40° C.under argon; this reaction solution was stirred for 3 hours. Aftercustomary workup by addition of saturated ammonium chloride solution,the reaction mixture was extracted with ethyl acetate, and the combinedorganic phases were dried over Na₂SO₄ and concentrated in a membranepump vacuum. After purification by column chromatography (ethylacetate/cyclohexane),2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(344 mg, 59%) is obtained as a yellow solid.

HPLC-MS: log P=3.23; Mass (m/z): 387; ¹H-NMR (d₆-DMSO): δ 8.14 (d, 1H),8.08 (s, 1H), 7.76 (d, 1H), 4.04 (s, 3H), 3.05 (q, 2H), 3.04 (s, 3H),1.21 (t, 3H).

EXAMPLE 4 (STEP C)

Synthesis of2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(310 mg, 0.57 mmol), dissolved in THF (3 ml), was added MeZnCl (2.0 M inTHF, 0.57 ml, 1.14 mmol) in the presence oftetrakis(triphenylphosphine)palladium(0) (66 mg, 0.05 mmol) at 40° C.under argon; this reaction solution was stirred for 5 hours. Aftercustomary workup by addition of saturated ammonium chloride solution,the reaction mixture was extracted with ethyl acetate, and the combinedorganic phases were dried over Na₂SO₄ and concentrated in a membranepump vacuum. After purification by column chromatography (ethylacetate/cyclohexane),2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(190 mg, 78%) is obtained as a yellow solid.

HPLC-MS: log P=3.36; Mass (m/z): 431; ¹H-NMR (d₆-DMSO): δ 8.08 (s, 1H),8.02 (d, 1H), 7.87 (d, 1H), 4.04 (s, 3H), 3.03 (q, 2H), 3.02 (s, 3H),1.19 (t, 3H).

EXAMPLE 5 (STEP C)

Synthesis of2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile

To2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-4-iodo-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(100 mg, 0.20 mmol), dissolved in pyridine (2 ml), was added CuCN (22mg, 0.24 mmol) at 80° C. under argon; this reaction solution was stirredfor 5 hours. After customary workup by addition of saturated sodiumchloride and ammonium chloride solutions, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),2-[6-chloro-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(99 mg, quantitative) is obtained as a yellow solid.

HPLC-MS: log P=3.84; Mass (m/z): 398; ¹H-NMR (d₆-DMSO): δ 8.73 (s, 11H),8.18 (d, 11H), 7.79 (d, 11H), 4.14 (s, 3H), 3.05 (q, 2H), 1.21 (t, 3H).

EXAMPLE 6 (STEP C)

Synthesis of2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile

To2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(752 mg, 1.03 mmol), dissolved in pyridine (4 ml), was added CuCN (112mg, 1.24 mmol) at 80° C. under argon; this reaction solution was stirredfor 3 hours. After customary workup by addition of saturated sodiumchloride and ammonium chloride solutions, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(473 mg, 88%) is obtained as a yellow solid.

HPLC-MS: log P=3.87; Mass (m/z): 442; ¹H-NMR (d₆-DMSO): δ 8.73 (s, 1H),8.06 (d, 1H), 7.91 (d, 1H), 4.14 (s, 3H), 3.06 (q, 2H), 1.21 (t, 3H).

EXAMPLE 7 (STEP C)

Synthesis of2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-chloro-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(258 mg, 0.47 mmol), dissolved in pyridine (2 ml), was added CuCl (57mg, 0.57 mmol) at 80° C. under argon; this reaction solution was stirredfor 5 hours. After customary workup by addition of saturated sodiumchloride and ammonium chloride solutions, the reaction mixture wasextracted with ethyl acetate, and the combined organic phases were driedover Na₂SO₄ and concentrated in a membrane pump vacuum. Afterpurification by column chromatography (ethyl acetate/cyclohexane),2-[6-bromo-3-(ethylsulfanyl)pyridin-2-yl]-4-chloro-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(209 mg, 58%) is obtained as a yellow solid.

HPLC-MS: log P=4.18; Mass (m/z): 452; ¹H-NMR (d₆-DMSO): δ 8.39 (s, 1H),8.07 (d, 1H), 7.90 (d, 1H), 4.07 (s, 3H), 3.04 (q, 2H), 1.20 (t, 3H).

Examples of Further Possible Conversions of Compounds of the Formula(III) to Compounds Effective as Pesticides Oxidation Synthesis of2-[6-chloro-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile

2-[6-Chloro-3-(ethylsulfanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(99 mg, 0.24 mmol) in dichloromethane (2 ml) was initially charged in aflask equipped with a magnetic stirrer bar. Formic acid (57 mg, 1.24mmol) and 35% hydrogen peroxide (169 mg, 1.73 mmol) were then added andthe mixture was stirred overnight at 25° C. The reaction mixture wascooled to 25° C. and a dilute HCl solution was then added (to pH 3-4). Alittle water and a sodium bisulfite solution were added to the reactionmixture followed by a sodium chloride solution and 20% sodiumbicarbonate solution, the mixture was extracted with dichloromethane(3*50 ml) and dried over anhydrous sodium sulfate. Following filtration,the solvent was removed under reduced pressure. The crude product waspurified by chromatography, which gave2-[6-chloro-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(94 mg, 83%) as a white solid.

MH⁺: 430; ¹H-NMR (400 MHz, d₆-DMSO) δ ppm: 1.22 (t, 3H), 3.71 (q, 2H),4.06 (s, 3H), 8.17 (d, 1H), 8.59 (d, 1H), 8.76 (s, 1H).

Cross-Coupling Synthesis of2-[3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(Compound No. 1)

2-[6-Chloro-3-(ethylsulfonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(83.6 mg, 0.19 mmol) in anhydrous dioxane (4 ml) was initially chargedin a dry, argon-filled 25 ml Schlenk flask, equipped with a magneticstirrer bar and a septum. 1H-1,2,4-triazole (16.1 mg, 0.23 mmol),caesium carbonate (95.1 mg, 0.29 mmol),9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (11.3 mg, 0.02 mmol) andbis(dibenzylideneacetone)palladium(0) (5.6 mg, 0.01 mmol) were thenadded and the mixture was stirred at 80° C. for 3 h. Saturated aqueoussodium chloride solution (25 ml) was added to the reaction mixture whichwas extracted with ethyl acetate (3*50 ml) and dried over anhydroussodium sulfate. Following filtration, the solvent was removed underreduced pressure. The crude product was purified by chromatography,which gave2-[3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile(52.4 mg, 55%) as a white solid.

MH⁺: 463; ¹H-NMR (400 MHz, d₆-DMSO) δ ppm: 1.23 (t, 3H), 3.84 (q, 2H),4.19 (s, 3H), 8.37 (d, 1H), 8.475 (s, 1H), 8.79 (d, 1H), 8.80 (s, 1H),9.52 (s, 1H).

Compounds No. 2 and 3 were prepared analogously to compound No. 1.

Compound No. Structure 1

2

3

USE EXAMPLES

Myzus persicae—Oral TestSolvent: 100 parts by weight of acetone

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up to the desired concentration with water.

50 μl of the active ingredient formulation are transferred intomicrotitre plates and made up to a final volume of 200 μl with 150 μl ofIPL41 insect medium (33%+15% sugar). Subsequently, the plates are sealedwith parafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 4 ppm: 1, 2,3

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive ingredient formulation of the desired concentration.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha: 3

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 g/ha: 3

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 g/ha: 2

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active ingredient formularation of the desired concentration and,after drying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha: 1,2

Spodoptera frugiverda—Spray Test

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Leaf discs of maize (Zea mays) are sprayed with an active ingredientformulation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillar has beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha: 3

1. Method for preparing a compound of formula (II)

in which Q and Z are each independently halogen, A¹ is nitrogen, ═N⁺O⁻or ═C—R⁵, A² is —N—R⁶, oxygen or sulfur, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, amino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,(C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of aryl, hetaryl andheterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally bemono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, nitro, hydroxyl, amino, carboxy,carbamoyl, aminosulfonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,(C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,(C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulfoximino,(C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl and benzyl, R³ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl or(C₃-C₈)cycloalkylamino, R⁴ is hydrogen, cyano, halogen, nitro, acetyl,hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonylamino),or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁵ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)and R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl, comprising reacting, a), a compoundof formula (I)

in which Z, R¹, R³, R⁴, A¹ and A² are each as defined above, with anorganozinc base of the structure (NR^(a)R^(b))—Zn—R^(c) or(NR^(a)R^(b))₂—Zn, in which R^(c) is halogen or —O-pivaloyl and R^(a)and R^(b) together form a —(CH₂)₄—, —(CH₂)₅— or —(CH₂)₂O(CH₂)₂— group,where each of these groups may optionally be substituted by 1, 2, 3 or 4R^(d) radicals and R^(d) is selected from the group consisting ofmethyl, ethyl, n-propyl and isopropyl, to give a compound of formula(IVa) or formula (IVb),

in which Z, R¹, R³, R⁴, R^(c), A¹ and A² are each as defined above, andthis compound of formula (IVa) or (IVb) is reacted in b) with a compoundof the structure Q-V, in which V is halogen and Q has the abovementioneddefinition, to give the compound of formula (II).
 2. Method according toclaim 1, wherein Q is chlorine, iodine or bromine, Z is bromine,fluorine or chlorine, R^(c) is —O-pivaloyl, chlorine, bromine or iodine,A¹ is nitrogen, ═N⁺—O⁻ or ═C—R⁵, A² is —N—R⁶ or oxygen, R¹ is(C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₆)cycloalkylamino,(C₁-C₄)alkylcarbonylamino, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)haloalkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonylamino, or is(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl or(C₃-C₆)cycloalkyl, each of which is optionally mono- or disubstituted byidentical or different substituents from the group consisting of aryl,hetaryl and heterocyclyl, where aryl, hetaryl or heterocyclyl may eachoptionally be mono- or disubstituted by identical or differentsubstituents from the group consisting of halogen, cyano, carbamoyl,aminosulfonyl, (C₁-C₄)alkyl, (C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl and (C₁-C₄)alkylsulfimino, R³is hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, aminothiocarbonyl, (C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulfonyl,(C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,aminothiocarbonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino) or isphenyl or hetaryl, each of which is optionally mono- or disubstituted byidentical or different substituents, where (in the case of hetaryl) atleast one carbonyl group may optionally be present and where possiblesubstituents in each case are as follows: cyano, halogen, nitro, acetyl,amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl anddi(C₁-C₄)alkylaminosulfonyl, R⁴ is hydrogen, cyano, halogen, nitro,acetyl, hydroxyl, amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, aminothiocarbonyl, (C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulfonyl,(C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,aminothiocarbonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), isfurthermore phenyl or hetaryl, each of which is optionally mono- ordisubstituted by identical or different substituents, where (in the caseof hetaryl) at least one carbonyl group may optionally be present andwhere possible substituents in each case are as follows: cyano, halogen,nitro, acetyl, amino, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,NHCO—(C₁-C₄)alkyl((C₁-C₄)alkylcarbonylamino), R⁵ is hydrogen, cyano,halogen, nitro, acetyl, hydroxyl, amino, SCN, tri(C₁-C₄)alkylsilyl,(C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, aminothiocarbonyl, (C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulfonyl,(C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,aminothiocarbonyl or NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino) andR⁶ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)haloalkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkylthio-(C₁-C₄)alkyl or(C₁-C₄)alkylcarbonyl-(C₁-C₄)-alkyl.
 3. Method according to claim 1,wherein Q is chlorine, iodine or bromine, Z is bromine, fluorine orchlorine, R^(c) is —O-pivaloyl, chlorine, bromine or iodine, A¹ isnitrogen or ═C—R⁵, A² is —N—R⁶, R¹ is (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl or (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,R³ is hydrogen, halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl or(C₁-C₄)haloalkylsulfonyl, R⁴ is hydrogen, cyano, halogen, nitro,hydroxyl, amino, SCN, tri(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,cyano(C₃-C₈)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkylhydroxyimino,(C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl orNHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), is furthermore phenyl orhetaryl, each of which is optionally mono- or disubstituted by identicalor different substituents, where (in the case of hetaryl) at least onecarbonyl group may optionally be present and where possible substituentsin each case are as follows: cyano, halogen, (C₃-C₆)cycloalkyl,(C₁-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, aminosulfonyl,(C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), R⁵ is hydrogen, halogen,cyano or (C₁-C₄)alkyl and R⁶ is (C₁-C₄)alkyl or(C₁-C₄)alkoxy-(C₁-C₄)alkyl.
 4. Method according to claim 1, wherein Q isiodine or bromine, Z is bromine or chlorine, R^(c) is chlorine, bromineor iodine, A¹ is nitrogen or ═C—R⁵, A² is —N—R⁶, R¹ is methyl, ethyl,n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl,cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R³is fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl,fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl ortrifluoromethylsulfinyl, R⁴ is hydrogen, cyano, halogen, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl or NHCO—(C₁-C₄)alkyl((C₁-C₄)alkylcarbonylamino), R⁵ is hydrogen, fluorine, chlorine, bromineor cyano and R⁶ is methyl, ethyl, isopropyl, methoxymethyl ormethoxyethyl.
 5. Method according to claim 1, wherein Q is iodine orbromine, Z is bromine or chlorine, R^(c) is chlorine or bromine, A¹ isnitrogen, A² is —N—R⁶, R¹ is methyl, ethyl, n-propyl, isopropyl orcyclopropyl, R³ is trifluoromethyl or pentafluoroethyl, R⁴ is hydrogenand R⁶ is methyl.
 6. Method according to claim 1, wherein Q is iodine orbromine, Z is bromine or chlorine, R^(c) is chlorine, A¹ is nitrogen, A²is —N—R⁶, R¹ is ethyl, R³ is trifluoromethyl, R⁴ is hydrogen and R⁶ ismethyl.
 7. Method according to claim 1, wherein the organozinc base is acompound of formula (VI)(TMP)_(x)ZnCl_(2-x),  (VI) in which x is the number 1 or
 2. 8. Methodaccording to claim 1, wherein the organozinc base is present inconjunction with an alkali metal halide or alkaline earth metal halide,optionally lithium chloride and/or magnesium chloride.
 9. Methodaccording to claim 1, wherein the compound Q-V is an elemental halogen,optionally F₂, Cl₂, Br₂ or I₂.
 10. Method according to claim 1, whereinthe solvent is THF or N,N-dimethylformamide (DMF).
 11. Method accordingto claim 1, wherein a) is conducted at a temperature between 0° C. and80° C.
 12. Method according to claim 1, wherein b) is conducted at atemperature between 0° C. and 80° C.
 13. Method according to claim 1,wherein the compound of formula (II) is further reacted in c) to give acompound of formula (III)

in which X is cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino,SCN, tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₁-C₆)cycloalkyl(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkoxyimino, —N═C(H)—O(C₁-C₆)alkyl, —C(H)═N—O(C₁-C₆)alkyl,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbamoyl (including—NHCOO(C₁-C₆)alkyl, —N(C₁-C₆)alkylCOO(C₁-C₆)alkyl, —OCONH(C₁-C₆)alkyl or—OCON(C₁-C₆)dialkyl), (C₁-C₆)alkylcarbonylamino ((C₁-C₆)alkylCONH),(C₁-C₆)alkylurea (including —NHCONH(C₁-C₆)alkyl, and—NHCON(C₁-C₆)dialkyl) or is a saturated, partially saturated orheteroaromatic ring which is optionally mono- or polysubstituted byidentical or different substituents and in which at least one carbonatom is replaced by a heteroatom, or is an aromatic ring which is mono-or polysubstituted by identical or different substituents, where atleast one carbonyl group may optionally be present in each case andwhere possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₁-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₁-C₆)cycloalkyl(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkoxyimino, —N═C(H)—O(C₁-C₆)alkyl, —C(H)═N—O(C₁-C₆)alkyl,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or (C₁-C₆)alkylcarbonylamino.
 14. Methodaccording to claim 13, wherein X is cyano, halogen, nitro, acetyl,amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,(C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkoxyimino, —N═C(H)—O(C₁-C₄)alkyl,—C(H)═N—O(C₁-C₄)alkyl, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, (C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di(C₁-C₄)alkylaminosulfonyl,(C₁-C₄)alkylcarbamoyl (including —NHCOO(C₁-C₄)alkyl,—N(C₁-C₄)alkylCOO(C₁-C₄)alkyl, —OCONH(C₁-C₄)alkyl or—OCON(C₁-C₄)dialkyl), (C₁-C₄)alkylcarbonylamino ((C₁-C₄)alkylCONH) or(C₁-C₄)alkylurea (including —NHCONH(C₁-C₆)alkyl and—NHCON(C₁-C₆)dialkyl).
 15. Method according to claim 13, wherein X iscyano, halogen, nitro, acetyl, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy or(C₁-C₄)alkoxy-(C₁-C₄)alkoxy.
 16. Method according to claim 13, wherein Xis cyano, halogen, amino, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, ((C₁-C₄)alkoxy or(C₁-C₄)cyanoalkoxy.
 17. Method according to claim 1, wherein thereaction in c) is conducted at a temperature between 0° C. and 110° C.18. Method according to claim 1 wherein the compound of formula (II) isreacted with one or more organozinc reagents in the presence of acatalyst or with one or more metal salts.
 19. Compound of formula (IVa)

in which Q and Z are each independently halogen, A¹ is nitrogen, ═N⁺O⁻or ═C—R⁵, A² is —N—R⁶, oxygen or sulfur, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, amino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,(C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloalkyl, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of aryl, hetaryl andheterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally bemono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, nitro, hydroxyl, amino, carboxy,carbamoyl, aminosulfonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,(C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,(C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulfoximino,(C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl and benzyl, R³ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloakyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloakyl,halo(C₃-C₈)cycloakyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl or(C₃-C₈)cycloalkylamino, R⁴ is hydrogen, cyano, halogen, nitro, acetyl,hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonylamino),or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)akylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁵ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)and R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl.
 20. Compound of formula (IVb)

in which Q and Z are each independently halogen, A¹ is nitrogen, ═N⁺O⁻or ═C—R⁵, A² is —N—R⁶, oxygen or sulfur, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, amino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,(C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloakyl, each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of aryl, hetaryl andheterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally bemono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, nitro, hydroxyl, amino, carboxy,carbamoyl, aminosulfonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,(C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,(C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulfoximino,(C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl and benzyl, R³ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)akylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl or(C₃-C₈)cycloalkylamino, R⁴ is hydrogen, cyano, halogen, nitro, acetyl,hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonylamino),or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁵ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)and R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl.
 21. Compound of formula (II)

in which Q and Z are each independently halogen, A¹ is nitrogen, ═N⁺O⁻or ═C—R⁵, A² is —N—R, oxygen or sulfur, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloakyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, amino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,(C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloakyl, each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of aryl, hetaryl andheterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally bemono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, nitro, hydroxyl, amino, carboxy,carbamoyl, aminosulfonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,(C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,(C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulfoximino,(C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl and benzyl, R³ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxyl-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl or(C₃-C₈)cycloalkylamino, R⁴ is hydrogen, cyano, halogen, nitro, acetyl,hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsufinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsufonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonylamino),or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁵ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)and R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl.
 22. Compound of formula (III)

in which Q and Z are each independently halogen, A¹ is nitrogen, ═N⁺O⁻or ═C—R⁵, A² is —N—R⁶, oxygen or sulfur, R¹ is (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,(C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl, amino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, (C₃-C₈)cycloalkylamino,(C₁-C₆)alkylcarbonylamino, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonylamino,aminosulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl,di(C₁-C₆)alkylaminosulfonyl-(C₁-C₆)alkyl, or is (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₈)cycloakyl, each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of aryl, hetaryl andheterocyclyl, where aryl, hetaryl or heterocyclyl may each optionally bemono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, nitro, hydroxyl, amino, carboxy,carbamoyl, aminosulfonyl, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl,(C₁-C₆)alkoxy, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl, (C₁-C₆)alkylsulfimino,(C₁-C₆)alkylsulfimino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfimino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkylsulfoximino,(C₁-C₆)alkylsulfoximino-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfoximino-(C₂-C₆)alkylcarbonyl, (C₁-C₆)alkoxycarbonyl,(C₁-C₆)alkylcarbonyl, (C₃-C₆)trialkylsilyl and benzyl, R³ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloakyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloakyl,halo(C₃-C₈)cycloakyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl or(C₃-C₈)cycloalkylamino, R⁴ is hydrogen, cyano, halogen, nitro, acetyl,hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,(C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, NHCO—(C₁-C₆)alkyl, (C₁-C₆)alkylcarbonylamino),or is aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where (in thecase of hetaryl) at least one carbonyl group may optionally be presentand where possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁵ is hydrogen,cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)alkylthiocarbonyl,(C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylaminothiocarbonyl,di(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or —NHCO—(C₁-C₆)alkyl ((C₁-C₆)alkylcarbonylamino)and R⁶ is (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)haloalkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl, aminocarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkylamino-(C₁-C₆)alkyl, di(C₁-C₆)alkylamino-(C₁-C₆)alkyl or(C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl, and X is cyano, carboxyl, halogen,nitro, acetyl, hydroxyl, amino, SCN, tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl,(C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl,(C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkyl,(C₃-C₆)cyanocycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₆)cycloalkyl (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,(C₁-C₆)cyanoalkoxy, (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkoxyimino, —N═C(H)—O(C₁-C₆)alkyl,—C(H)═N—O(C₁-C₆)alkyl, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbamoyl (including—NHCOO(C₁-C₆)alkyl, —N(C₁-C₆)alkylCOO(C₁-C₆)alkyl, —OCONH(C₁-C₆)alkyl or—OCON(C₁-C₆)dialkyl), (C₁-C₆)alkylcarbonylamino ((C₁-C₆)alkylCONH),(C₁-C₆)alkylurea (including —NHCONH(C₁-C₆)alkyl, and—NHCON(C₁-C₆)dialkyl) or is a saturated, partially saturated orheteroaromatic ring which is optionally mono- or polysubstituted byidentical or different substituents and in which at least one carbonatom is replaced by a heteroatom, or is an aromatic ring which is mono-or polysubstituted by identical or different substituents, where atleast one carbonyl group may optionally be present in each case andwhere possible substituents in each case are as follows: cyano,carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri(C₁-C₆)alkylsilyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,(C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)halocycloalkyl, (C₃-C₆)cyanocycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkoxyimino, —N═C(H)—O(C₁-C₆)alkyl, —C(H)═N—O(C₁-C₆)alkyl,(C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di(C₂-C₆)alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino or (C₁-C₆)alkylcarbonylamino.